Potassium Carbonate → HCID 28574797, compound

HRID 1754993Notes

Reaction equation

HRID 1754993 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:19])([F:18])[CH2:9]OS(C(F)(F)F)(=O)=O.[Br:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=1[CH3:28]>CC#N>[Br:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][CH2:9][C:8]([F:19])([F:18])[F:7])=[CH:23][C:22]=1[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 233594-Bromo-3-methylanilineHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 28574797HCID 28574797, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (2.50 g, 18.1 mmol) and trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester (2.36 ml, 16.4 mmol) were added to a solution of 4-bromo-3-methylaniline (1.68 g, 9.03 mmol) in MeCN (39.0 ml) at room temperature, and the mixture was stirred at 80° C. overnight. The reaction mixture was concentrated under reduced pressure, and the resulting residue was then purified by silica gel column chromatography (hexane-ethyl acetate) to give (4-bromo-3-methyl-phenyl)-(2,2,2-trifluoro-ethyl)-amine (2.20 g, 91%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was then purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-08e49c761819435d8b1d2a0a009d00c0
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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